Upper Sugarloaf Key Fishing Charters

The best out of 263 charter fishing deals in Upper Sugarloaf Key - enter dates to check availability

Upper Sugarloaf Key Fishing Charters

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Top Fishing Charters in Upper Sugarloaf Key

Upper Sugarloaf Key: 263 fishing charters available

Showing 1 - 10
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16 ft

Up to 2 people

Held Fast Charters

4.9/5 (64 reviews)
Cudjoe Key (3 min drive from Upper Sugarloaf Key)
Embark on our specialized flats fishing charter in the serene beauty of the Florida Keys. Glide through emerald-green mangrove flats, surrounded by vibrant wildlife. With a focus on fly rods and light tackle, cast for tarpon, bonefish, permit, and more.

"A pleasure to be out on the flats for the first time.  Several schools and Dozens of Tarpon." —⁠ Manny,
Trips from
US $450
Trips from
US $450
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25 ft

Up to 4 people

Goliath Charters Summerland

4.8/5 (80 reviews)
Cudjoe Key (3 min drive from Upper Sugarloaf Key)
Welcome to Goliath Charters, your gateway to the fishing paradise of the Florida Keys. Led by Captain Craig Clopper, an experienced US Navy Veteran and certified captain, our 25ft Seavee boat is equipped to handle nearly any sea conditions.

"We took a 2 hrs fishing trip with Capt Craig He knew exactly where to go and after fast 15 min boat ride we were on a big Tarpon splashing left and right." —⁠ Wioletta,
Trips from
US $200
Trips from
US $200
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Meet the Captain
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16 ft

Up to 2 people

Michael O’Brien Charters

4.8/5 (45 reviews)
Cudjoe Key (3 min drive from Upper Sugarloaf Key)
Come on down to the Florida Keys and enjoy world-class flats fishing with Michael O’Brien Charters. Going out of Cudjoe Gardens Marina, Michael will show you why fishing in the Keys draws in anglers from all over the country.

"Flats expert!" —⁠ Nicholas,
Trips from
US $700
Trips from
US $700
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17 ft

Up to 2 people

Dry Bones Fishing Charters

5.0/5 (3 reviews)
Cudjoe Key (3 min drive from Upper Sugarloaf Key)
Dry Bones Fishing Charters is here to show you the stunning waters of Cudjoe Key.

"My wife and I went on a half day fishing trip with captain Blake of Dry Bones Charters and had an awesome time!" —⁠ Evelyn, Florida
Trips from
US $600
Trips from
US $600

Angler's choice

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17 ft

Up to 2 people

Fish'n Fly - Florida Keys

4.9/5 (28 reviews)
Sugarloaf Keys (2 min drive from Upper Sugarloaf Key)
The warm, tropical climate and the outstanding beauty of the Florida Keys attracts visitors from around the world and Fish Finder adventures is here to show you why.

"Big Cuda, Black tip & Lemon sharks…great day. Capt knows how to get you on fish!" —⁠ Thomas,
Trips from
US $250
Trips from
US $250

Angler's choice

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26 ft

Up to 6 people

Lower Keys Offshore Adventures

4.9/5 (105 reviews)
Little Torch Key (14 min drive from Upper Sugarloaf Key)
Based in Big Pine Key, Lower Keys Offshore Adventures offer family-friendly offshore, snorkeling, and reef fishing trips. The charters are run by Capt. Allen Prince, who has over 20 years of experience exploring the waters around the Florida Keys.

"We had an incredible experience fishing with Captain Allen! From the moment we stepped on board, he was kind, knowledgeable, and exceptionally patient—especially with our child, who is new to fishing." —⁠ Kelsey,
Trips from
US $550
Trips from
US $550
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32 ft

Up to 6 people

Salt Therapy Charters

4.8/5 (87 reviews)
Summerland Key (9 min drive from Upper Sugarloaf Key)
Experience the breathtaking waters of the Lower Florida Keys whether it’s fishing, relaxing and swimming at the beautiful sandbars, snorkeling at the reef, or witnessing a gorgeous sunset with Salt Therapy Charters.

"Captain and Mate were great, I would highly recommend" —⁠ Scott,
Trips from
US $800
Trips from
US $800
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17 ft

Up to 2 people

Salty Sloth Flats Guide

Sugarloaf Keys (2.5 miles from Upper Sugarloaf Key)
Book your next trip with Salty Sloth Flats Guide and find out what makes the fishing in the Lower Keys so unique.
Trips from
US $500
Trips from
US $500

Angler's choice

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22 ft

Up to 4 people

Key West Fishing Connection

5.0/5 (149 reviews)
Stock Island (19 min drive from Upper Sugarloaf Key)
Based out of Stock Island, Key West Fishing Connection invites you to join them for an extraordinary adventure you’ll cherish in your memories for years to come.

"Captain Dan is the MAN!!! We wanted to catch big fish and he did not disappoint hooking up to our first shark before we knew it." —⁠ Brandon, Florida
Trips from
US $499
Trips from
US $499
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24 ft

Up to 4 people

Reel Nice

5.0/5 (4 reviews)
Sugarloaf Keys (2.5 miles from Upper Sugarloaf Key)
Reel Nice invites you for an enjoyable day of fishing in Key West, Florida. Join Captain Marc Kennedy on the city’s inshore and offshore waters and have a great time chasing the numerous and various fish that call these grounds home.

"Christmas vacation fans will know the quote. If you know, you know." —⁠ Dustin, Oklahoma
Trips from
US $600
Trips from
US $600

Top deep sea fishing trips in Upper Sugarloaf Key

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Top-rated family fishing trips in Upper Sugarloaf Key

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Half-day fishing trips in Upper Sugarloaf Key

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Top Targeted Species in Upper Sugarloaf Key

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Top Types of Fishing in Upper Sugarloaf Key

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Top Fishing Techniques in Upper Sugarloaf Key

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Frequently Asked Questions about Fishing Charters in Upper Sugarloaf Key

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Frequently Asked Questions about Fishing Charters in Upper Sugarloaf Key

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Upper Sugarloaf Key Fishing Calendar

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Featured photos from Upper Sugarloaf Key

What anglers said about fishing in Upper Sugarloaf Key

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How did anglers rate fishing charters in Upper Sugarloaf Key?

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Nearby Fishing Destinations

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